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200 Deep Personal Questions To Ask A Guy And A Girl

200 Deep Personal Questions To Ask A Guy And A Girl

These deep personal questions are designed to get to know a person you’re interested in, to find more information that will help you get close to them and try to sweep them off their feet.  

If your questions are good and interesting, you can really capture a person’s attention, which will definitely get you to the answers you want to hear.

These types of questions don’t have to be used only when you’re interested romantically in someone, you can also use them when you are new to a group and you want to fit in. They can also be used as online dating questions.

Sure, these questions are not something you can’t live without but wouldn’t it be nice to have an ice-breaker line when you meet someone new or when you’re in an awkward situation and you want to save the day by breaking an awkward silence.

Deep personal questions to ask a guy:


1. What do you think about online dating and would you ever try something like that?

2. Would you make a bucket list and try to complete it within a year?

3. What’s your ideal weekend?

4. Since we’re sharing things, what’s the craziest thing you’ve ever done?

5. What’s your relationship deal-breaker and is there something you just can’t stand?

6. Have you ever lost someone close to you?

7. Off the top of your head without too much thinking, what’s your biggest regret in life?

8. Do you have a person in your life you can talk to?

9. What’s your opinion about online dating on Tinder?

10. What phase in your life do you think you are at right now?


11. What’s your idea of a perfect life?

12. I’m a big, old bookworm—do you have a favorite book or movie?

13. If you could choose a location anywhere in the world to go for a vacation, where would it be and what’s your idea of a perfect vacation?

14. Are you happy with yourself, or is there something you would like to change, something that you’re not proud of?

15. Do you like the way you look?

16. How much time do you spend getting ready before going out? And be honest!

17. Do you believe in God or in any kind of a higher force or do you think that there is nothing out there?

18. What do you think about where we go when we die and is there something more, or is this it?

19. Is your personality extrovertive or introvertive?

20. Have you ever dated a crazy chick?

21. What’s the worst thing a girlfriend did to you?

22. What’s the best thing that happened to you in life?

23. What’s the worst thing that happened to you in life?

24. Where do you see yourself 10 years from now?

25. What does the word success mean to you?

26. What does the word love mean to you?

27. What’s the most romantic thing you’ve ever done for a girl and how did she react?

28. Are looks more important to you than brains?

29. Are you a boob or a butt guy?

30. What do you think—can enemies be friends?

31. Can men and women be friends without sexual tension between them?

32. Have you ever cheated on someone?

33. How would you react if someone cheated on you, would you forgive them and why?

34. Would you raise your kid exactly like your parents raised you, or would you do something different, and if the answer to the latter is yes, what would it be?

35. Do you stay in contact with your exes?

36. Do you lose your temper easily?

37. If you fell in love and that person had to move to another country, would you follow her?

38. Is it easier for you to sometimes put your thoughts down on paper and do you feel better afterward?

39. Do you think life gives you second chances?

40. Would you ever stay in a toxic relationship?

41. What is the thing that makes you the most nervous?

42. Are you an adrenaline junkie?

43. Do you like music?

44. What three words would you use to describe your best friend?

45. Do you have a pet?

46. Do you like being single?

47. What’s your biggest fear?

48. Can you name the three most important people in your life?

49. Who is your role model, who do you look up to?

50. Where do you go when you want to be alone?

51. What’s your favorite beer?

52. What was your craziest drinking experience?

53. If you could change one thing to make the world a better place, what would it be?

54. What’s your favorite sport to watch and to play?

55. What’s your favorite meal?

56. On a scale of 1 to 10, how weird are you?

57. NSYNC or Backstreet Boys?

58. How good of a person are you on a scale of 1 to 10?

59. What’s your dream job?

60. What’s your favorite food?

61. Are you a dog or a cat person?

62. What’s the closest you’ve ever come to being arrested?

63. If you were to catch a goldfish, which three wishes would you have?

64. Who’s your favorite Marvel character and why?

65. Do you believe in destiny?

66. If you had the ability to travel through time, to which period would you go and why?

67. If you could, what would you change about your past?

68. If you had a task to ask a person just one question, what would it be?

69. What are your priorities in life?

70. Money or love?

71. What’s your favorite female body part?

72. How many times have you been in love?

73. When you are in a bad mood, do you prefer whether someone tries to cheer you up or leaves you alone?

74. What is the one question you will never give me an answer to?

75. What advice would you give to the younger version of yourself?

76. Do you want to have kids?

77. Would you ever forgive yourself for doing a girl wrong?

78. Would you ever hide your girlfriend from your friends?

79. What is the one thing you’re the most insecure about?

80. Do you think you’re going to be a good parent?

81. Do you keep a journal?

82. Are you musical?

83. Are you into politics?

84. What’s the weirdest conversation you’ve ever had with someone?

85. What’s your favorite movie scene?

86. What’s your perfect date outfit?

87. When did you lose your virginity?

88. What’s your middle name?

89. Is there something about your life that you just keep ignoring because you aren’t ready to face it?

90. What’s the one thing that can always bring a smile to your face?

91. What is the one thing you can’t live without?

92. What’s the biggest decision you ever had to make?

93. What was the most stressful moment of your life?

94. Would you ever break the law?

95. What’s the most inspiring thing you saw someone do?

96. What empowers you?

97. Have you ever been depressed?

98. Do you believe in heaven and hell?

99. Are you a workaholic?

100. Would you ever put your life in someone else’s hands and if you would, who would that person be?

Deep personal questions to ask a girl

1. Do you believe in true love?

2. What’s the one thing you would never forgive anyone for?

3. When you set boundaries, do you stick to them?

4. What do you love the most about yourself?

5. What do you hate the most about yourself?

6. How do you think people see you?

7. What is the one thing that would make you unconditionally happy?

8. If you could be someone else for a day, who would you be?

9. Do you think you could endure the pressure of being famous?

10. Who is your favorite cartoon character?

RELATED: 310+ Romantically Cute Questions To Ask Your Boyfriend


11. Which Spice Girl are you?

12. What are you scared of the most?

13. Which personality trait would you like to get rid of?

14. Which personality trait are you most proud of?

15. What does your ideal relationship look like?

16. If you had to, how would you describe your perfect man?

17. What is the strangest thing you ever did?

18. What is the most annoying thing about you?

19. What is the most beautiful thing about you?

20. Would you ever forgive a man who cheated on you?

21. Who would you give your life for?

22. Was there a moment in your past that defined you as the person you are today?

23. What do you imagine your future to be like?

24. In your opinion, what’s the key to a successful relationship?

25. What is the definition of happiness for you?

26. When you are angry or sad, do you like to be left alone?

27. Do you think that the first impression matters?

28. What do you think your first impression is like?

29. What is your guilty pleasure?

30. What’s the treatment you expect from your partner?

31. What is the one thing you’re most embarrassed about?

32. Is there something about your past you wished never happened?

33. What’s the one responsibility you wish you didn’t have?

34. What’s the one thing people always misunderstand about you?

35. Do you want to have kids?

36. What kind of a mother would you be?

37. Who are you closer to, your mom or your dad?

38. Would you risk your life for your BFF?

39. Do you think relationship-wise that you have learned from your mistakes?

40. What’s your biggest dream?

41. Are you happy with your life right now?

42. What do you think about online dating?

43. What does your dream wedding look like?

44. If you could go anyplace you wanted right now, where would you go?

45. What do you want to do before you die?

46. Is there an activity that calms you?

47. What makes you the most anxious?

48. What is the most touching movie scene you’ve ever seen?

49. On a scale of 1 to 10, how much do you like puppies?

50. Where’s your hiding place when you need to be alone?

51. Has a man ever broken your heart?

52. Have you ever been in a toxic relationship?

53. What does a man have to do for you to trust him?

54. If you could choose one, what was the weirdest date you’ve been on?

55. What’s the cheesiest line a guy has tried to use on you?

56. Would you rather a guy be honest with you even if it hurt, or lie to you to spare your feelings?

57. Do you think you’re living your life to the fullest?

58. What’s the one thing you wish to do but you know that you’ll never actually do it?

59. What’s the biggest lie you’ve ever told?

60. What is the one thing that can always make you cry?

61. Cats or dogs?

62. What’s your happiest childhood memory?

63. What gives your life meaning?

64. Is there a person you hate and why?

65. Has anyone ever betrayed you?

66. Do you like skiing?

67. What is the best possible vacation for you?

68. What’s your favorite drink?

69. What’s your favorite food?

70. Do you have a tattoo?

71. What’s the craziest thing you’ve ever done with your friends and would you do it again?

72. Have you ever been in trouble with the police?

73. Have you ever been so drunk that your friends had to carry you home?

74. Is there something embarrassing that you’re really good at?

75. What’s the nicest thing you’ve ever done for anyone?

76. Where do you go when you need to recharge?

77. What’s your pet’s name?

78. What does your perfect date look like?

79. How long did the shortest date you were on last?

80. What’s your biggest turn-on?

81. What’s your biggest turn-off?

82. Have you ever cheated on a guy?

83. How many boyfriends have you had?

84. Are you religious?

85. Who are the five most important people in your life and why?

86. When was the first time you fell in love?

87. If you had to write a book about your life, what would the title be?

88. Have you ever cried tears of joy?

89. What does the word home mean to you?

90. What is the most common dream you have?

91. What does your dream home look like?

92. Do you believe in the afterlife?

93. Do you like art?

94. What is your favorite song?

95. What’s your favorite party song?

96. Have you ever dreamed of being immortal?

97. Do you like to travel?

98. What’s the farthest you’ve been away from home?

99. What’s the one thing you can’t live without?

100. I like you, do you like me?